The Four-Hour Rule: Chicago Weekend Getaway to Milwaukee

Stipulated: the perfect travel time for a three-day weekend getaway is four hours. More, and you waste your vacation. Less, and you’re still near home. Hence our series, The Four-Hour Rule, dedicated to revealing the best destinations that are far away, yet still close to home.

Ah, Milwaukee.

It’s long been a favorite getaway — mostly because it doesn’t even take a full tank of gas to get there: we’re talking just 90 miles on I-94.

So this winter, we suggest packing up the car — or heck, grabbing yourself an Amtrak ticket — and setting your sights north.

Yes, there will be beer. Also bratwurst. Probably some cheese. Did we mention beer? Milwaukee was once home to Pabst, Schlitz, Blatz and Miller — though today, only the latter remains.

But even teetotalers can have a great time in Brew City. Here’s where to go.

The Journeyman Hotel
The Journeyman Hotel opened last summer in the Milwaukee’s historic Third Ward neighborhood, which stands as the city’s main hub for restaurants, art galleries and a riverwalk that gives Chicago a run for its money. While the 158-room hotel technically falls under the Kimpton umbrella, its vibe is far from cookie-cutter. The hotel lays on the boutique ambience with subway-tiled showers and leather-and-wood details that nod to the district’s industrial past. The friendly concierge will hook you up with a leather backpack and a rundown of the area’s best spots — though if it’s nice out, you may want to stay put and linger on the hotel’s rooftop.

Journeyman Hotel, 310 E. Chicago St. (map)

Also check out: Iron Horse Hotel

Third Coast Provisions
Milwaukee, like the rest of the Midwest, is known for its meat, but to spend a weekend here and only eat brats is too cliché for you, sir. Proof is in Chef Andrew Miller’s just-opened seafood mecca Third Coast Provisions. The beers are all brewed in the Midwest, though the seafood lineup takes a more global approach (a good thing). There’s salmon from British Columbia and oysters from the coasts, though one oyster dish gets the local treatment (it’s topped with pastrami and beer).

Where are my lunch options, you say? Try Bavette La Boucherie, a butcher shop-slash-sandwich spot that’s just around the corner from The Journeyman. Get the braised beef sandwich. Or, for more options, head to the Milwaukee Public Market, where you’ll find seafood and sandwich vendors — and cheese. We recommend loading up on the Wisconsin delicacy for your ride home.

Third Coast Provisions, 724 N. Milwaukee St. (map)

Also check out: The Tandem

Bryant’s Cocktail Lounge
Bryant’s Cocktail Lounge is a study in the unexpected. First, the velvet-lined, dimly lit bar is located on a residential street on the city’s southwest side, in what looks more like a single-family home than a famous cocktail bar. Second, the bar has no menus. Just tell your server what you fancy, and they’ll return with a drink crafted to your taste buds. They’ve got a track record of getting it right — hence why it’s been a mainstay of the Milwaukee drinking scene since 1938.

Bryant’s Cocktail Lounge, 1579 S. 9th St. (map)

Also check out: Burnhearts

Milwaukee Art Museum
Known to locals as MAM, the Milwaukee Art Museum is worth a visit for its iconic architecture alone. Three distinct architectural wonders make up the museum: the War Memorial Center, which is in the shape of a floating cross; Cudahy Gardens, the well-manicured grounds; and a far-out wing-like structure (that opens and closes) called “the Calatrava,” after its Spanish architect. Once you ogle the outside, head in to make a dent in checking out the 30,000-plus works of art.

Milwaukee Art Museum, 700 N. Art Museum Dr. (map)

Also check out: Walker’s Point Center for the Arts

Lakefront Brewery
No Milwaukee itinerary would be complete without a stop at a brewery. If you’re up for a tour (and you should be), you’ve got options. Our recommendation is to head to Lakefront Brewery. The tour guides are funny, the beer is tasty and the waterfront location can’t be beat — though technically, it’s the Milwaukee River and not Lake Michigan like the name implies.

Still thirsty? Hit another tour at MillerCoors, Sprecher Brewing Company or Milwaukee Brewing Company.

Lakefront Brewery, 1872 N. Commerce St. (map)

Also check out: Good City Brewing Co.

Royal Enfield
Milwaukee is the birthplace of Harley-Davidson, so it may seem blasphemous to head to another motorcycle shop. But paying a visit to the Royal Enfield’s new showroom is worth any risk of feeling disloyal toward the OG. The handsome Third Ward showroom (which, fun fact, is also the company’s North American headquarters) is in the old Mitchell Leather factory and stocks motorcycles and biking accessories galore for you to peruse.

Royal Enfield, 226 N. Water St. (map)

Also check out: Harley-Davidson Museum

And your packing list …
You’ve got your itinerary, now ya need the gear. A proper motorcycle jacket will hunt. Also a sturdy beer opener for all that brew you’ll be drinking. Below, everything you need for your weekend in Milwaukee.

Clockwise from top left: Deus Ex Machina Addict Asymmetry Jacket ($1,325); Bottle Opener Carabiner ($89); Mr Porter x Todd Snyder Crewneck ($145); Alpine Division McKenzie Bag ($90); Woolrich Packer Boot ($224); Shinola Runwell Chronograph ($750)